Bile acids with cyclopropane-containing side chain. 2. Synthesis and properties of 3.alpha.,7.beta.-dihydroxy-22,23-methylene-5.beta.-cholan-24-oic acid (2-sulfoethyl)amide

Abstract

The preparation of 3 alpha,7 beta-dihydroxy-22,23-methylene-5 beta-cholan-24-oic acid (2-sulfoethyl)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid "cyclopropylog" (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.